Top Tuscany Wine Tasting & Winery Tours

Q: Got any more Tuscany trip ideas?

We sure do. Check out our curated lists of hand-picked Tuscany Tours. Top 10 Tuscany 2026 Senior-friendly tours Tuscany The best tours and activities for culture lovers in Tuscany Top Day Trips from Tuscany Things to do in Tuscany this summer View all Tuscany Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Tuscany?

Based on our sales data over the past year, the most popular styles of tours and activities in Tuscany are: Tuscany Cultural & Theme Tours Tuscany Luxury & Special Occasions Tuscany Luxury Tours Tuscany Cultural Tours Tuscany Historical & Heritage Tours View all tour styles in Tuscany →

Florence Cooking Class: Lasagna, Tiramisu & Market or Pasta Class

Join one of the most authentic Florence Cooking Class experiences and choose between two unforgettable culinary adventures. Learn from professional local chefs in Florence's first …More

Florence, Italy

4.9 (1,842)

Florence Cooking Class: Lasagna, Tiramisu & Market or Pasta Class

Join one of the most authentic Florence Cooking Class experiences and choose between two unforgettable culinary adventures. Learn from professional local chefs in Florence's first...

5 hours Free Cancellation

4.9 (1,842)

from
$55

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable …More

Florence, Italy

4.9 (1,877)

Tuscany Small Group Tour: Siena & San Gimignano with Winery Lunch

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable...

10 hours Free Cancellation

4.9 (1,877)

from
$170

Florence Small-Group Pasta Class Seasonal Ingredients with Wine

This is not just a cooking class — it’s a fully immersive culinary experience inside a real cooking school in Florence, where every detail is …More

Florence, Italy

5.0 (525)

Florence Small-Group Pasta Class Seasonal Ingredients with Wine

This is not just a cooking class — it’s a fully immersive culinary experience inside a real cooking school in Florence, where every detail is...

2 hours 30 minutes Free Cancellation

5.0 (525)

from
$125

Tuscan Countryside Vespa Tour from Florence with Wine

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL …More

Florence, Italy

4.9 (619)

Tuscan Countryside Vespa Tour from Florence with Wine

Escape from the crowded streets of the city to see life as a local as you zip around the stunning Tuscan countryside on a REAL...

5 hours Free Cancellation

4.9 (619)

from
$194

Florence Pasta & Tiramisu Cooking Class with Unlimited Wine

Learn the art of authentic Italian cuisine in the heart of Florence’s historic center. Guided step by step by expert chefs, you’ll learn how to …More

Florence, Italy

4.9 (569)

Florence Pasta & Tiramisu Cooking Class with Unlimited Wine

Learn the art of authentic Italian cuisine in the heart of Florence’s historic center. Guided step by step by expert chefs, you’ll learn how to...

2 hours 30 minutes Free Cancellation

4.9 (569)

from
$34

From Florence: San Gimignano, Wine Tasting & Cooking Class

Escape the bustle of Florence and discover the authentic beauty of Tuscany on this small-group countryside tour. Travel through rolling hills and vineyards as you …More

Florence, Italy

4.5 (579)

From Florence: San Gimignano, Wine Tasting & Cooking Class

Escape the bustle of Florence and discover the authentic beauty of Tuscany on this small-group countryside tour. Travel through rolling hills and vineyards as you...

11 hours 30 minutes Free Cancellation

4.5 (579)

from
$181

Tuscany in One Day: Pisa, Siena, San Gimignano & Chianti Lunch

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. …More

Florence, Italy

4.8 (2,653)

Tuscany in One Day: Pisa, Siena, San Gimignano & Chianti Lunch

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine....

12 hours Free Cancellation

4.8 (2,653)

from
$74

Florence Food & Wine Tour: Tuscan Tastings in the Historic Center

Gelato, Chianti wine, olive oil, and authentic Tuscan dishes—this Florence food tour is a feast for the senses. Discover the flavors of Cucina Povera, learn …More

Florence, Italy

4.9 (546)

Florence Food & Wine Tour: Tuscan Tastings in the Historic Center

Gelato, Chianti wine, olive oil, and authentic Tuscan dishes—this Florence food tour is a feast for the senses. Discover the flavors of Cucina Povera, learn...

2 hours 30 minutes Free Cancellation

4.9 (546)

from
$97

Tuscany Vespa Tours Through the Hills of Chianti

There is nothing more exciting and unique than driving a vespa through the Tuscan hills. Live “La Dolce Vita” with us. Our Tuscany Vespa Tours …More

Florence, Italy

5.0 (575)

Tuscany Vespa Tours Through the Hills of Chianti

There is nothing more exciting and unique than driving a vespa through the Tuscan hills. Live “La Dolce Vita” with us. Our Tuscany Vespa Tours...

6 hours Free Cancellation

5.0 (575)

from
$184

Chianti Wine Tour for Small Groups: 3 Family Wineries & Lunch

Embark on an unforgettable Chianti tour guided by an experienced Italian sommelier. Discover hidden, family-owned wineries nestled in the Tuscan countryside, far from the typical …More

Florence, Italy

5.0 (12)

Chianti Wine Tour for Small Groups: 3 Family Wineries & Lunch

Embark on an unforgettable Chianti tour guided by an experienced Italian sommelier. Discover hidden, family-owned wineries nestled in the Tuscan countryside, far from the typical...

8 hours Free Cancellation

5.0 (12)

from
$250

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover …More

Siena, Italy

4.9 (1,035)

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Brunello di Montalcino, a collector’s favorite, is internationally recognized as one of the best Italian red wines. On this full-day guided tour from Siena, discover...

9 hours Free Cancellation

4.9 (1,035)

from
$217

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore …More

Florence, Italy

4.6 (4,518)

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore...

11 hours Free Cancellation

4.6 (4,518)

from
$90

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan …More

Florence, Italy

4.9 (1,271)

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

A day trip exploring Tuscany with visits to 2 wineries. Taste 8 different types of wine, three extra virgin olive oils, balsamic vinegar and Tuscan...

7 hours Free Cancellation

4.9 (1,271)

from
$85

From Florence: Tuscany Wine & Oil Tour with typical Tuscan Meal

Discover Tuscany’s wine paradise on a tour from Florence, crafted by Towns of Italy. Travel in a luxury Mercedes minivan through the Chianti Classico region, …More

Florence, Italy

4.7 (947)

From Florence: Tuscany Wine & Oil Tour with typical Tuscan Meal

Discover Tuscany’s wine paradise on a tour from Florence, crafted by Towns of Italy. Travel in a luxury Mercedes minivan through the Chianti Classico region,...

7 hours Free Cancellation

4.7 (947)

from
$101

Tuscany Vespa & Wine Tour, lunch, medieval villages, wine tasting

This all-inclusive small group Vespa moped tour is a great way to discover the beauty of the Tuscan wine countryside and its magic.. …More

Florence, Italy

5.0 (517)

Tuscany Vespa & Wine Tour, lunch, medieval villages, wine tasting

This all-inclusive small group Vespa moped tour is a great way to discover the beauty of the Tuscan wine countryside and its magic.....

6 to 7 hours Free Cancellation

5.0 (517)

from
$228

Pisa, Siena, San Gimignano with Lunch & Wine Tasting at a Winery

There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gimignano …More

Florence, Italy

4.6 (5,072)

Pisa, Siena, San Gimignano with Lunch & Wine Tasting at a Winery

There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gimignano...

12 hours Free Cancellation

4.6 (5,072)

from
$52

A Brunello Cooking Class with Vineyards View Winery

Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance …More

Siena, Italy

5.0 (352)

A Brunello Cooking Class with Vineyards View Winery

Brunello Cooking Class with Chef Alexandra - Cooking class with a view in the morning, followed by Lunch pairing with Brunello wines! With the guidance...

4 hours Free Cancellation

5.0 (352)

from
$296

Bolgheri: Classic Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and make a wine-tasting for a 75 minutes experience tour. Nestled 3mi (5 km) from the village center of …More

Livorno, Italy

4.8 (138)

Bolgheri: Classic Wine Tasting with Winery Tour

Visit "Terre del Marchesato" vineyards, winery and make a wine-tasting for a 75 minutes experience tour. Nestled 3mi (5 km) from the village center of...

1 hour 15 minutes Free Cancellation

4.8 (138)

from
$23

Brunello Wine Tour and Val D'Orcia Landscape

I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where …More

Arezzo, Italy

5.0 (100)

Brunello Wine Tour and Val D'Orcia Landscape

I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where...

4 hours Free Cancellation

5.0 (100)

from
$253

Private Day Trip Siena, San Gimignano and Chianti from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through …More

Florence, Italy

5.0 (271)

Private Day Trip Siena, San Gimignano and Chianti from Florence

• EXPERIENCE FOR YOUR PRIVATE GROUP • Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (271)

from
$142

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Tuscany Wine Tasting & Winery Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Tuscany Wine Tasting & Winery Tours are:

What are the best kid-friendly options for Tuscany Wine Tasting & Winery Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Tuscany Wine Tasting & Winery Tours are:

View all kid-friendly Tours →

Which Tuscany Wine Tasting & Winery Tours have Instant Confirmation?

Tuscany Wine Tasting & Winery Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Which Tuscany Wine Tasting & Winery Tours have Free Cancellation?

Tuscany Wine Tasting & Winery Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Tuscany Wine Tasting & Winery Tours have Hotel Pickup?

No problem. These Tuscany Wine Tasting & Winery Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Tuscany trip ideas?

What are the most popular styles of Tours and Activities in Tuscany?